Journal of Organic Chemistry 2012-01-20

Stereoselective α-quaternization of 3-methoxycycloalk-2-enones via 1,4-diastereoinduction of alkoxy dienolates.

Gamal A I Moustafa, Yasumasa Kamada, Tetsuaki Tanaka, Takehiko Yoshimitsu

Index: J. Org. Chem. 77(2) , 1202-7, (2012)

Full Text: HTML

Abstract

The alkylation of dienolates generated from 3-methoxycycloalk-2-enones having a 3'-hydroxyl alkenyl chain provides the corresponding quaternized cycloalkenones in a highly diastereoselective manner. The high degree of stereocontrol in the α-quaternization possibly implies intervention of a rigid chelating transition state that allows an efficient 1,4-asymmetric induction to take place.

Related Compounds

Related Articles:

Synthesis and structure-activity relationship of cyclopentenone oximes as novel inhibitors of the production of tumor necrosis factor-α.

2014-07-01

[Bioorg. Med. Chem. Lett. 24(13) , 2807-10, (2014)]

Expanding the scope of asymmetric electrophilic atom-transfer reactions: titanium- and ruthenium-catalyzed hydroxylation of beta-ketoesters.

2004-04-20

[Proc. Natl. Acad. Sci. U. S. A. 101(16) , 5810-4, (2004)]

Discovery of orally efficacious melanin-concentrating hormone receptor-1 antagonists as antiobesity agents. Synthesis, SAR, and biological evaluation of bicyclo [3.1. 0] hexyl ureas. McBriar MD, et al.

[J. Med. Chem. 49(7) , 1202-1207, (2012)]

More Articles...